Hamilton 1883: Very 2009

"Our customers in Houston would come to us for their dress shirts but would go somewhere else for their sport shirts," says Hamilton co-owner Kelly Hamilton. "We wanted that business, too." Enter 1883, her company's first ready-to-wear offering. Named after Hamilton's founding year, the line is handmade from paper patterns in the same Houston factory as Hamilton's celebrated custom shirting, using the same Italian double-ply fabrics. But while the craftsmanship is old-school, the look, which was developed with help from consultant Stephen Watson, is anything but. The fit is both slimmer and slightly shorter than a traditional dress shirt, and unlined collars and cuffs—the shirts also come prewashed—add up to an appealingly fitted-yet-rumpled look. Throw in some cool details pulled from the company archives (I loved the pencil pocket and sleeve tabs), and I'd say you've got a pretty good business plan to corner the sport-shirt market in Texas—and just about anywhere else.

Available now at the Hamilton flagship store, 5700 Richmond Ave., Houston, (713) 264-8800, and at hamilton1883.com.